|Table of Contents|

Synthesis kinetics of isobornyl acrylate by addition reaction of acrylic acid and camphene(PDF)


Research Field:
Publishing date:


Synthesis kinetics of isobornyl acrylate by addition reaction of acrylic acid and camphene
ZHANG TingjianTANG JihaiFEI ZhaoyangCHEN XianCUI MifenQIAO Xu
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Nanjing Tech University,Nanjing 210009,China
acrylic acid camphene isobornyl acrylate(IBOA) SO3H-SBA-15 kinetics
The addition reaction of camphene with acrylic acid to prepare isobornyl acrylate(IBOA)was carried out over sulfonic acid functionalized SBA-15(SO3H-SBA-15).Kinetic experimental data were obtained with the eliminated external diffusion at the stirring speed of 600 r/min.The α-terpinene,limonene,fenchene derived from the isomerization of camphene catalyzed by SO3H-SBA-15 were treated as isomeric olefins,and the corresponding acrylic esters generated by addition of acrylic acid and isomeric olefins were regarded as isomeric acrylate.From the established pseudo-first-order kinetic model,the parameters were regressed.The reaction heat of addition esterification of acrylic acid and camphene,isomerization of camphene,and esterification of isomeric olefins was -9.41,-31.32 and -13.39 kJ/mol,respectively.The correlated results agreed well with the experimental data,and the statistic test results indicated that the kinetic model was reliable.


[1] CHEN L J,BAO Z B,FU Z R,et al.Synthesis and characterization of novel cross-linking poly(butyl acrylate-co-isobornyl methacrylate)colloids prepared via semi-continuous seeded emulsion polymerization [J].Colloid journal,2015,77(3):374.
[2] 马国章,闫涛,吴建兵,等.叔胺型聚氨酯丙烯酸酯的合成及其光固化性能研究[J].现代化工,2010,30(4):44.
[3] WILLIAMS R M,KHUDYAKOV I V,PURVIS M B,et al.Direct and sensitized photolysis of phosphine oxide polumerization photoinitiators in the presence and absence of a model acrylate monomer:a time resolved EPR,cure monitor,and photo DSC study[J].The journal of physical chemistry B,2000,104(44):10437.
[4] CHEUNG K C,WONG W L,SO M H,et al.A dinuclear ruthenium catalyst with a confined cavity:selectivity in the addition of aliphatic carboxylic acids to phenylacetylene[J].Chemical communication,2013,49(7):710.
[5] NEWMAN M B.Process of making ester of acrylic and methacrylic acid:US 3087962[P].1963-04-30.
[6] 陈慧宗,杨义文,刘永根,等.纳米固体超强酸S2O82-催化合成正、异冰片酯的研究[J].有机化学,2005,25(11):1490.
[7] DIJS I J,GEUS J W,JENNESKENS L W.Effect of size and extent of sulfation of bulk and silica-supported ZrO2[J].The journal of physical chemistry B,2003,107(48):13403.
[8] DE MEIRELESA L P,ROCHA K A D,KOZHEVNIKOV I V,et al.Esterification of camphene over heterogeneous heteropoly acid catalysts:synthesis of isobornyl carboxylates[J].Applied catalysis A:general,2011,409:82.
[9] LI L,LIU Y,YU S T,et al.Hydration of α-pinene homogenous catalyzed by acidic polyether-modified ammonium salt ionic liquid in “microreactor”[J].Research on chemical intermediates,2015,41(4):2407.
[10] CASAS E,VAN G R,ESCOLA J M.Polymerization of ethylene with(nBuCp)2ZrCl2 supported over mesoporous SBA-15 functionalized with sulfonic acid groups[J].Applied catalysis A:general,2012,437:44.
[11] SASIDHARAN M,BHAYMIK A.Selective conversion of nitroalcohols to nitroolefins over sulfonic acid functionalized mesoporous SBA-15 material[J].Journal of molecular catalysis A:chemical,2013,367:1.
[12] ZHOU F,TANG J H,FEI Z Y,et al.Efficient cyclohexyl acrylate production by direct addition of acrylic acid and cyclohexene over SBA-15-SO3H[J].Journal of porous materials,2014,21(2):149.
[13] 王莹淑,郑辉东,吴方棣,等.离子交换树脂催化合成甲基丙烯酸异冰片酯[J].福州大学学报(自然科学版),2013,41(6):1121.
[14] CHIMAL-VALENCIA O,ROBAU-SANCHEZ A,COLLINS-MARTINEZ V,et al.Ion exchange resins as catalyst for the isomerization of α-pinene to camphene[J].Bioresource technology,2004,93(2):119.


Last Update: 2017-05-31